tert-Butanol → N-(t-Butoxycarbonylsulfamoyl)-N-(2-benzyloxy-4-phenoxyphenyl)glycine methyl ester

HRID 1642626Notes

Reaction equation

HRID 1642626 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].[CH3:13][O:14][C:15](=[O:39])[CH2:16][NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:20][C:19]=1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:13][O:14][C:15](=[O:39])[CH2:16][N:17]([S:2](=[O:4])(=[O:3])[NH:5][C:6]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])[C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:20][C:19]=1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 66756720(2-Benzyloxy-4-phenoxyphenylamino)acetic acid methyl ester

Product 1

HCID 66757056N-(t-Butoxycarbonylsulfamoyl)-N-(2-benzyloxy-4-phenoxyphenyl)glycine methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of chlorosulfonyl isocyanate (0.274 g, 1.93 mmol) in DCM (2 mL) is added dropwise a solution of t-butanol (0.143 g, 1.93 mmol) in 1 mL DCM. The solution is stirred at ambient temperature for 45 min. A solution of (2-benzyloxy-4-phenoxyphenylamino)acetic acid methyl ester (0.50 g, 1.38 mmol) and triethylamine (0.278 g, 2.75 mmol) in DCM (1 mL) is added dropwise. The mixture is stirred at ambient temperature for 30 min., then washed with Water. The organic phase is dried over Na2SO4 and the solvent removed under reduced pressure. The residual oil is purified by flash chromatography using DCM to elute N-(t-butoxycarbonylsulfamoyl)-N-(2-benzyloxy-4-phenoxyphenyl)glycine methyl ester as an oil: 1H NMR (CDCl3) δ 7.50 (d, J=8.84 Hz, 1H), 7.34-7.23 (m, 8H), 7.08 (t, 1H), 6.92-6.88 (m, 2H), 6.50 (d, J=2.53 Hz, 1H), 6.43 (dd, J=11.12, 2.53 Hz, 1H), 5.22 (s, 2H), 5.01 (s, 2H), 3.62 (s, 3H), 1.36 (s, 9H); MS (M−H)−=541.

Workup

  1. stirringThe mixture is stirred at ambient temperature for 30 min.
  2. washwashed with Water
  3. dry with materialThe organic phase is dried over Na2SO4
  4. customthe solvent removed under reduced pressure
  5. customThe residual oil is purified by flash chromatography
  6. washto elute N-(t-butoxycarbonylsulfamoyl)-N-(2-benzyloxy-4-phenoxyphenyl)glycine methyl ester as an oil

Sources & evidence

ORD record
ord-be5908b095be4fa0a54edd0c20bb6594
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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